
%0 Journal Article
%A Latif, Tariq 
%A Javed, Tariq 
%A Lynch, Daniel E. 
%A Pryce, Robert J. 
%A Byriel, Karl A. 
%T X-Ray Crystal Structure of <emph type="2">N</emph>-[3-(Diethylaminomethyl)-4- hydroxyphenyl]acetamide and its Hydrochloride Salt. Two Forms of an Important Precursor in the Synthesis of Anti-Tuberculosis Drugs
%J Australian Journal of Chemistry
%D 1999/11/11
%V 52
%N 9
%P 909-913
%K 
%R https://doi.org/10.1071/CH99040
%U https://www.publish.csiro.au/paper/CH99040 
%X N-&#91;3-(Diethylaminomethyl)-4-hydroxyphenyl&#93;acetamide (dmhpa) and its hydrochloride salt (dmhpaH+ Cl&#8722;) have been prepared and their X-ray crystal structures determined. The structure of dmhpa comprises an intramolecular hydrogen bond between the hydroxy group and the diethylaminomethyl nitrogen and an intermolecular association between adjacent N-acetamide groups resulting in a non-centrosymmetric interdigitated &#8216;V&#8217; polymeric network. Quantitative non-linear optical measurements on a powdered sample of dmhpa revealed a second harmonic signal of two-thirds the intensity of a urea standard. In contrast, the hydrochloride salt is formed via protonation of the diethylaminomethyl nitrogen and resides in a complex hydrogen-bonded network which involves not only the free chloride ion but also one water molecule per dmhpaH+ Cl&#8722;. 
